What is the most interesting question you can ask to get to know someone?
11.06.2025 11:31
Do you like the “69” position? Do you prefer to be on top or bottom?
11- List at least 5 things on your bucket list. Have you done any of them already?
Model/Photographer Police/Criminal
In my experience, British people are fat, ugly and arrogant. Why is it and can it be changed?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
85~ If you gave me a “free Pass” to have me do anything for one hour, what would you want me to do to you?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
I would allow you to do it… What would you do to me?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Master/Slave Boss/Maid
14- What is an embarrassing moment in your life? How about your most embarrassing?
32- What's your greatest talent? Can I see it right now?
53~ How much can you tell me about the one thing you are most passionate about?
40 Father’s Day Gifts He’ll Wanna Brag About - BuzzFeed
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
39~ What are your love languages?
28~ What are some things that turn on? What is your biggest turn on?
Why is there no evidence of a multiverse theory?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
92~ Everyone needs a “safe” word. What is yours?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
The New Twist In Regeneron's 23andMe Bankruptcy Buyout - Investor's Business Daily
7- What are your thoughts on religion? Is there an afterlife?
36- Do you play video games? What is your favorite? Do you a least favorite?
10- List 5 of your top pet peeves.
New Report: Flooding is Now NYC’s Biggest Threat - Boro Park 24
40~ What’s the weirdest place you’ve ever had sex?
61~ How willing would you be to try new sexual positions?
1- What was your first impression of me? Has it changed?
Do humans know everything they need to know?
51~ Are you willing to play adult games with your partner?
The Ice Breaker Questions
Will you kiss after your partner has gone down on you? Swallow or spit semen?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
7-What do I do in bed that drives you wild? How about, what turns you off?
75~ If your partner wants an orgasm/have sex when you don't desire to have sex, how do you plan to deal with their needs?
Why do men like women gold diggers?
71~ Would you give your partner a hand or foot job? Would you receive one?
10~ How many dates are necessary before you to have sex with someone?
76~ Have you had a threesome? Care to Share?
What do you respect the most about Elon Musk?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Can you Deep Throat? Do you like the taste of yourself?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Why do flat-Earthers think the Earth is flat?
92~ Have you ever had or have an STD? How many? What was it?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
* Give a rating for each one (0-100)
If NO, would you ever have one? Would it be with 2 men or 2 women?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
*** Questions About Me ***
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
29- How superstitious are you?
59~ Have/do you masturbate? How often? What do you use? (Toys, Phone sex, Erotica, Hard Core, shower/water, etc) Would you, while your partner watches?
83~ How do you feel about Porn?
36~ What is your favorite time of day to have sex/make love?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
*** Deal Breaker Questions ***
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
1~ How old were you when you had your first kiss? Who? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
19~ Who/when was your first “heartbreak”?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
13- How about having a certain hair cut/style?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
42~ What’s your biggest regret in life?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Do you think this brought you closer together?
9- What’s your favorite season and why? What’s your least favorite?
52~ What are your hobbies?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
50~ How many children do you have? What are their ages?
14- What's your favorite dessert? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
These go from easy to answer, to OMG, you really want to know that?! to some serious thought. Take your time and have fun with this. The past is the past… it got you two here together…
20- What’s your favorite candy? What’s your least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
11- How about if they like a certain sports team? 12-How about drinking too much?
9~ How many times over your lifetime do you think you have had sex so far?
23- What is your dream job? What was it as a child?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
52~ Are you willing to make “those types” of bets with your partner?
18- How often do you drink alcohol? What is your favorite drink?
19- Do/have you smoked? What do you prefer? How often?
What is your favorite toy? Ever wanted to try a specific toy?
If YES, was it with 2 men or 2 women? Did you enjoy it?
How about if they talk dirty and/or call you names?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
What is your view on sex? Meaning, When/Where/ How often/
Family Relation Age Play
3- What Superhero or Superpower would you want to be/have?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Do you like it when they show and tell you what they want?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
If you win, what will you make them do?
What would you say to prove to yourself that it was really you?
1- What’s your favorite animal? Do you a least favorite?
2~ How old were you when you got to 2nd base? (Tongue kissing, breast feeling, or outside the clothes genital contact) Who? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
70~ Would/do you have/like anal sex?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Would you read them together?
21- What's your favorite way to spend a weekend or time off?
12- What’s your favorite food? What’s your least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
15- What's your favorite saying? What word or phrase is your least favorite?
Escort/Client Job Applicant/Hiring Manager
34- Ever been to a concert? What was your favorite? Who would you like to see?
13- What is the craziest/scariest thing you've ever done?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
11- What's your favorite restaurant? What’s your least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
27- What was/ is nickname? Does it have a meaning behind it?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Does the thought excite you? Care to share?
37- Do you like your name? If you could change it, what would you change it too?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
28- What are some things that people do that irritate you?
17- What’s your favorite holiday? What’s your least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
34~ Do you like the lights on or off during sex?
Would /have you ever given your partner a lap dance and Striptease?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Do you have a favorite? Is it ok if your partner does?
15- What bad habit do you wish you could quit? Do you have any addictions?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
23~ What do you believe is required to have a successful and healthy relationship? (This is important, take your time, and really think about this)
8- What's your favorite flavor of ice cream? Do you a least favorite?
Any that are a turn off?
44~ Care to share something about yourself that no one else knows about you?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
81~ Do you have any kinks and/or fetishes?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
45~ How do you feel about me blindfolding you? How about blindfolding me?
How many times do you think you have “made love”?
*** Random Questions ***
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Doctor/Nurse Stripper/Client
41~ What are you best at in bed? What do you think you are not so good at? Anything you want to get good at?
8- What are your thoughts on politics?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
18~ Who/when was your first “crush”?
40~ If you could go back in time, and relive your life, with the knowledge you have now, what age would you go back to and why?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
82~ Do you have any fantasies involving Role-Playing?
14- Do you have a “Deal Breaker”, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
50~ Where would you like to be touched more? Do you have a place that you want to be touched, that no one has, or has only happened a couple times? How about less?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
3- What’s your favorite smell? Do you a least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Do you watch it? What is your favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couples’ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETC…)
12- What is the weirdest thing you've ever eaten?
What have you learned about me that was new and/or surprising?
Would you ever want to be woken up with oral and/or intercourse?
Nurse/Patient Celebrity/Fan
22~ What is the best pickup line anyone has ever used on you? What was the worst?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
84~ How do you feel about reading/listening to adult stories?
How many partners have you had oral sex with? Who? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
4- For a pet, Cat, dog or other?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Any that are a turn off?
If yes, what?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
51~ What tends to bring a smile to your face?
49~ How many times have you been married? Why did they end?
Please share Did you stop?
13~ Is there a difference between, making love, having sex, and fucking?
33- Beach or Mountains? Or is there another place to like better?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Would you allow me to clean every part of your body with my soapy hands and fingers?
25~ How do you feel about PDA? (Public Display of Affection)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
How old are you? Male or Female?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
15~ Have you ever been “in love”? Who? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
47~ What would be your dream job and why?
7- What if a person smells a certain way? 8- How about smoking?
If you say it, I will stop, and we can talk about it when you are ready.
26~ What side of the bed do you sleep on?
11- Is there something you would like me to do, in any area of our relationship that I have not done, or you want more of?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Will you cheat again? How can, you be sure? Define what cheating is to you.
2- What’s your favorite color? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
*** Questions about Relationships/Past ***
48~ Have you ever paid or been paid for sex?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
85~ If I gave you a “Free Pass” for you to do anything to me for one hour, knowing that no matter what you did,
What have you learned about yourself that you did not before this?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
62~ Have you used adult toys?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
9- Is there something you’ve always wanted to ask me but you’re afraid?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
That one or two things that made you go hmmmm, OMG or wow!
You know that I will be 100% truthful, so ask.
Get this wrong and this could mean the end… :-) some funny, some not…
Would you do it again, and would you rather 2 females or 2 males?
Nothing too Serious
Have you ever? Care to Share?
38~ Share your most embarrassing sexual memory?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
22- What is your favorite childhood memory? What is your least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
29~ What are some things that turn you off? What is your biggest turn off?
What is your favorite position? Why?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
21~ What was the best date you ever went on? What has been the worst?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
5~ When you first started having sex, was it what you thought it would be?
What do you dislike about me? I asked you to be 100% honest.
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
89~ Do you like taking showers together?
A comprehensive questionnaire, this should be a fun exercise to get to know each other. Try to give as much detail as possible when answering questions. You can go through this together and talk about each question or fill out the questionnaire as completely as you can and once you are done, go through each question together. If you have been together for a while, it is also fun to try to answer the questions for your partner. Remember this should be fun, so if you do not wish to answer a question you can “PASS” and not answer. Both should answer honestly and without judgement. (This is important, without judgement) I hope this helps you get closer and strengthens your relationship… You can learn a lot about the other person… and yourself…
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
48~ Do you have any siblings? Are you close to your family?
13- What’s your favorite drink? What’s your least favorite?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
17- Have you ever done drugs? Which ones? How often?
9- If you could have three wishes, what would they be? Why?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
5- Have you ever been hypnotized? Would you allow yourself to be?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
3- Should Pluto still be considered a planet? 4- How about smoking?
30~ What's something unexpected that turns you on?
Repairman/Lonely Wife Virgin/Experienced
Over time has your thoughts on sex changed?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What was the longest? What was the shortest?
31- If given a chance to be immortal, would you take it? Why?
Teacher/Student Stranger/One Night Stand
*** What’s Your Favorite…? ***
Would you mind if your partner watched it? How about together vs alone?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
How well do you know me? And some of your thoughts about me
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
67~ Do you like it when your partner moans and/or is vocal during sex?